Exploring the hidden potential of a methoxy substituted HBT derivative as an efficient example of coupling of AIE and ESIPT processes and as an energy harvesting platform

Abstract

A methoxy substituted HBT derivative 2-(benzo[d]thiazol-2-yl)-6-methoxyphenol (TMP) showed coupling of AIE and ESIPT, underwent FRET with Rhodamine B and detected Sulfide in pure water by ratiometry.

ESIPT‐based AIE luminogens: Design strategies, applications, and mechanisms

“…Another widely used backbone that is used to construct ESIPT‐based AIEgens is 2‐(2′‐hydroxyphenyl)benzothiazole (HBT, Scheme 2I with X = S), which is a typical ESIPT fluorophore bearing an intramolecular hydrogen bond O─H···N and show AIE properties by virtue of RIM mechanism. [ 31, 36, 42, 45, 46, 56, 59, 63, 73, 76, 81, 100, 103, 108, 120–123, 126, 131 , 180–194 ] The emissions of HBT derivatives are easily tunable and extended to the red region, making them advantageous to be applied in bioimaging. [ 103, 126, 192, 193, 195 ] In addition, a few of ESIPT‐based AIEgens based on 2‐(2′‐hydroxyphenyl)benzimidazole (HBI, Scheme 2I with X = NH), [ 196 ] and 2‐(2′‐aminophenyl)benzothiazole (ABT, Scheme 2J) [ 52, 63, 90, 101, 114, 197 ] have been reported.…”

Structural isomerism induces pH dependent AIE-coupled ESIPT: an in-depth spectroscopic exploration with application in amine vapor sensing

“…Our group has been involved in the spectroscopic dissection of the underlying photophysical properties of various self-designed probes showing coupling of Intramolecular Charge Transfer (ICT) with ESIPT, competition of ESIPT between potential acceptor H-bonding sites as well as probes showing coupling of AIE and ESIPT. 27–31…”

Excited‐State Intramolecular Proton Transfer (ESIPT) for Optical Sensing in Solid State

“…First, we focus on the study of fluorescent small organic ESIPT molecules in the solid state and the optical sensing mechanism for ions, neutral guest molecules and physical effects. As illustrated in Figure 1, the ESIPT fluorophores mentioned in this article include 2-(2'-hydroxyphenyl)benzimidazole (HBI), [12] 2-(2'-hydroxyphenyl) benzothiazole (HBT), [13][14][15][16][17][18][19][20][21][22] 2-(2'-hydroxyphenyl)benzoxazole (HBO), [23] N-salicylideneaniline, [24,25] 2-(1H-pyrazol-3-yl)phenol, [26,27] 2-(2H-1,2,3-triazol-2-yl) phenol, [28] and so on. [29][30][31][32][33][34][35][36] The various mechanisms of ESIPTrelated optical sensing in the solid state will be discussed and summarized below.…”

“…Guchhait et al synthesized a HBT based Sensor 15 which coupled ESIPT with AIE, and could serve as an efficient S 2fluorescent sensor. [19] Sensor 15 displayed brilliant yellow emission in aqueous solution for the staking of molecular by van der Waals interaction. After the addition of S 2-, the stacked state was destroyed on account of Sensor 15+S2-with excellent water solubility.…”

“…Reproduced with permission. [19] Copyright 2019, The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.…”